CA1063620A - Process for the preparation of hydrazodicarboxylic acid amide - Google Patents
Process for the preparation of hydrazodicarboxylic acid amideInfo
- Publication number
- CA1063620A CA1063620A CA238,760A CA238760A CA1063620A CA 1063620 A CA1063620 A CA 1063620A CA 238760 A CA238760 A CA 238760A CA 1063620 A CA1063620 A CA 1063620A
- Authority
- CA
- Canada
- Prior art keywords
- water
- reaction
- acid amide
- urea
- hydrazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000008569 process Effects 0.000 title claims abstract description 31
- 150000001408 amides Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004202 carbamide Substances 0.000 claims abstract description 33
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 31
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims abstract description 30
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- 229910021529 ammonia Inorganic materials 0.000 description 13
- 230000035484 reaction time Effects 0.000 description 12
- 239000012452 mother liquor Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000013505 freshwater Substances 0.000 description 4
- 150000002429 hydrazines Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012431 aqueous reaction media Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- ULUZGMIUTMRARO-UHFFFAOYSA-N (carbamoylamino)urea Chemical compound NC(=O)NNC(N)=O ULUZGMIUTMRARO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 229940059913 ammonium carbonate Drugs 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229920001821 foam rubber Polymers 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- QEHKBHWEUPXBCW-UHFFFAOYSA-N nitrogen trichloride Chemical compound ClN(Cl)Cl QEHKBHWEUPXBCW-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742452016 DE2452016C3 (de) | 1974-11-02 | Verfahren zur Herstellung von Hydrazodica rbonamid | |
| DE19752532380 DE2532380C3 (de) | 1975-07-19 | Verfahren zur Herstellung von Hydrazodicarbonamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1063620A true CA1063620A (en) | 1979-10-02 |
Family
ID=25767918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,760A Expired CA1063620A (en) | 1974-11-02 | 1975-10-31 | Process for the preparation of hydrazodicarboxylic acid amide |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5839152B2 (it) |
| BR (1) | BR7507176A (it) |
| CA (1) | CA1063620A (it) |
| ES (1) | ES442260A1 (it) |
| FR (1) | FR2289495A1 (it) |
| GB (1) | GB1465019A (it) |
| IE (1) | IE42284B1 (it) |
| IN (1) | IN141781B (it) |
| IT (1) | IT1048048B (it) |
| LU (1) | LU73694A1 (it) |
| NL (1) | NL7512738A (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775330A (zh) * | 2012-07-24 | 2012-11-14 | 杭州海虹精细化工有限公司 | 一种尿素法生产水合肼过程中副产盐碱的回收处理方法 |
-
1975
- 1975-10-13 GB GB4181975A patent/GB1465019A/en not_active Expired
- 1975-10-30 NL NL7512738A patent/NL7512738A/xx not_active Application Discontinuation
- 1975-10-31 BR BR7507176*A patent/BR7507176A/pt unknown
- 1975-10-31 IE IE2372/75A patent/IE42284B1/en unknown
- 1975-10-31 JP JP50130562A patent/JPS5839152B2/ja not_active Expired
- 1975-10-31 CA CA238,760A patent/CA1063620A/en not_active Expired
- 1975-10-31 LU LU73694A patent/LU73694A1/xx unknown
- 1975-10-31 ES ES75442260A patent/ES442260A1/es not_active Expired
- 1975-10-31 FR FR7533475A patent/FR2289495A1/fr active Granted
- 1975-10-31 IT IT52021/75A patent/IT1048048B/it active
-
1976
- 1976-01-22 IN IN132/CAL/76A patent/IN141781B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1465019A (en) | 1977-02-16 |
| IT1048048B (it) | 1980-11-20 |
| IE42284L (en) | 1976-05-02 |
| ES442260A1 (es) | 1977-07-01 |
| FR2289495A1 (fr) | 1976-05-28 |
| IN141781B (it) | 1977-04-16 |
| LU73694A1 (it) | 1976-08-13 |
| FR2289495B1 (it) | 1980-08-14 |
| IE42284B1 (en) | 1980-07-16 |
| JPS5168526A (en) | 1976-06-14 |
| BR7507176A (pt) | 1976-08-03 |
| JPS5839152B2 (ja) | 1983-08-27 |
| NL7512738A (nl) | 1976-05-04 |
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